Ranking All 16 of Chandler Bing’s Love Interests on ‘Friends’
Netflix is back with a new documentary about our beloved sweater-vested comedian, Chandler Bing (Matthew Perry), or, more accurately, the man who brought him to life. The One About Matthew Perry explores Perry’s rise to fame, his signature role, and his years-long struggle with addiction. The documentary features testimonials from his sister, Mia Perry Bowick; lifelong best friend Roger Castillo; creative collaborators; and recovery advocates.
To celebrate the man, the myth, the legend, we’re taking a trip down memory lane to revisit Chandler Bing’s bumpy love life over the course of 10 seasons of Friends. Unlike Joey (Matt LeBlanc), Chandler was never exactly known for his Casanova ways, and most of his relationships were short-lived and (not-so) sweet — except for his romance with Monica (Courteney Cox), of course. From revenge sex to ethical non-monogamy, here are all of Chandler Bing’s love interests, ranked.
Friends, All Seasons, Streaming Now, HBO Max
The One About Matthew Perry, October 27, Netflix
16. Jade
This is a classic messy Chandler dating story. A random woman (Brittney Powell) calls Chandler’s phone, mistakenly believing it belongs to a man named Bob, whom she used to date. After hearing that she takes aerobics, that her legs were featured on the latest James Bond poster, and that she loves to party, Chandler is intrigued — and decides to pretend to be Bob.
He arranges a date with her, only to stand her up before swooping in when she’s disappointed and stealing the date for himself. Chandler thinks they have a great time, but there’s one problem: Jade later calls the real Bob and reveals that she found Chandler’s sexual performance awkward and bumpy. Oops.
15. Dana
Chandler had a minor fling with Dana (Bess Meyer) back in college, so he reaches out when he learns she’s now directing a movie —because Joey wants an audition. Dana gets the wrong idea and assumes Chandler is still in love with her, so she tries to let him down gently.
Chandler insists that’s not the case, but then realizes he can use the misunderstanding to his advantage and asks Dana for that audition. It works! Chandler gets Joey the audition… only for Joey to not get the part.
14. Jill
We know nothing really happened between these two, but we couldn’t resist including Jill Goodacre because, honestly, the name alone is iconic. Chandler finds himself trapped in an ATM vestibule with the popular Victoria’s Secret model and immediately recognizes her.
What follows is a surprisingly fun and lighthearted ordeal: Chandler chokes on gum, speaks in code to Joey, and learns how to flip a pen around his head. And while there’s no romance to speak of, Jill does give him a quick kiss at the end.
The funniest moment, though, comes when Chandler turns to the camera and begs for a copy of the tape. Honestly, relatable.
13. Julie
We never actually see Chandler’s relationship with Julie (Lauren Tom), only the fallout. When Monica mentions the upcoming wedding in public, Julie overhears and sarcastically wishes her “good luck.” It turns out Julie was Chandler’s camp girlfriend —they dated for two summers when they were around 15, before Chandler broke things off because she had gained 145 pounds between the second and third summer.
Monica is understandably horrified, particularly given her own history with weight, and insists Chandler apologize to Julie. When they meet again, Julie is annoyed to see him, but agrees to hear him out. The problem? She had no idea that Chandler had broken up with her because of her weight gain.
After an excruciatingly awkward pause, Chandler declares, “Well, I guess my work here is done.” Yikes.
12. Danielle
We hear about Danielle (Lynn Clark) long before we actually meet her. After a first date that Chandler describes as “one of the greatest first dates of all time,” he’s convinced they’re a perfect match. They could completely be themselves, he says, without having to play any games.
Naturally, Chandler refuses to call her straight away because he’s terrified of seeming “needy.” Instead, he sits around waiting for her to call, slowly losing his mind as the phone stubbornly refuses to ring.
Then, at the end of the episode, Danielle turns up at Central Perk looking for Chandler. Turns out, she had been trying to call him, but she’d written down his number incorrectly. When she finally got it right, there was no answer, likely because Chandler had accidentally turned his phone off.
And Chandler’s response? He decides she’s being “needy” for going to all that effort to find him. Honestly, men.
11. Susie
Susie “Underpants” Moss! How could we ever forget her?! Honestly, we’d put solid money on Susie being a Scorpio because that girl can hold a grudge. Susie is a former childhood classmate of Chandler’s whom he runs into on Joey’s film set, where she’s working as a makeup artist.
Unbeknownst to Chandler, Susie has been nursing a serious grudge ever since he pantsed her in front of the entire school. The pair starts dating and hooking up (she’s committed to the cause), before Susie finally gets her revenge on a double date, leaving Chandler stranded in a bathroom with no clothes.
Yikes. But with Julia Roberts playing Susie? Absolutely iconic.
10. Marjorie
Sleeping with Marjorie (Christina Moore) was the problem… get your head out of the gutter. We mean the actual sleep part.
Chandler meets Marjorie at a sleep clinic after bringing Joey in to get his snoring under control. Initially, they’re both interested in each other, but Joey falls asleep and misses his shot. Chandler and Marjorie hit it off, but there’s one small problem: Marjorie is at the clinic because she sleep-talks.
And unfortunately for Chandler, her sleep talking isn’t exactly cute. It soon escalates into full-on screaming, proving to be a little too much for him. Turns out, even Chandler has his limits.
9. Ginger
Chandler and Joey have way too much overlap when it comes to the women they date. This time, it’s Ginger (Sherilyn Fenn), who briefly dated Joey before things went awry when he accidentally threw her prosthetic leg into the fire, mistaking it for a wooden log.
Chandler initially struggles with Ginger’s prosthetic leg, even cutting their makeout session short because he can’t get past it. But he eventually overcomes his hang-up, only for Ginger to discover Chandler’s third nipple. She immediately makes a run for it.
Not cool, Ginger! Not the nubbin.
8. Mary-Angela
You don’t sleep with your bestie’s family! Come on, Chandler, this is basic etiquette. Still sad about a breakup, Chandler makes out with one of Joey’s sisters during his birthday party. It’s Jell-O shot-fueled, so we can’t be too mad at him. The real problem? He doesn’t remember which sister. And Joey has seven sisters.
Long story short, Chandler pretends he wants something serious, heads over to her house, and promptly kisses the wrong sister. He gets a well-deserved punch from one of Joey’s other sisters, and that’s that.
Not his finest moment by any means.
7. Joanna
You should never dip your pen in the company’s inkwell — or whatever the modern version is for laptops. Don’t plug into the office’s charger? Either way, workplace romances are complicated, especially when your new fling happens to be your best friend’s boss.
Joanna (Alison La Placa) isn’t Chandler’s boss —she’s Rachel’s — but that doesn’t make things any less awkward. Chandler meets her when he comes to pick Rachel up for lunch (and, naturally, score some freebies), and the pair soon starts seeing each other.
We love the kink positivity, including Joanna handcuffing Chandler to a filing cabinet when they hook up in her office. Chandler, however, is less enthusiastic about the arrangement and eventually ends up arguing with Rachel to get him free.
All in all, the whole relationship leaves Chandler in an incredibly awkward position. Maybe keep your love life and your workplace separate, guys.
6. Nina
This time, Chandler goes for someone at his own company, and somehow it’s even worse — but also a hilarious storyline. His boss tells him he needs to fire Nina (Jennifer Grant), but Chandler struggles to do it because he finds her so attractive. In a moment of panic, he accidentally asks her out instead, and the pair starts dating. Surprisingly, they seem to get on really well.
Things quickly unravel when Chandler’s boss discovers that Nina hasn’t been fired. Chandler panics and claims she had a psychotic break, meaning they couldn’t fire her— and that she wouldn’t remember being fired anyway. It’s an absolutely terrible plan, but somehow he keeps the lie going until everyone starts avoiding Nina and eventually tells her the truth.
Chandler later tells the gang that she took it “pretty well… except for the stapler thing,” before raising his bandaged hand.
Abuse of power? Bad. Gorgeous woman and hilarious storyline? Good.
5. Aurora
Talk about a storyline that was ahead of its time! Aurora (Sofia Milos) is a married polyamorous woman whom Chandler briefly dates in Season 1. She’s stunning, interesting, great company, and Chandler initially loves the idea of their no-strings-attached arrangement. But it doesn’t take long for his jealousy to kick in, especially when he struggles with how little time they spend together.
Things get even more complicated when Chandler discovers that Aurora doesn’t just have a husband — she has a boyfriend, too. Honestly, where does she find the time?!
Points for Friends showcasing ethical non-monogamy, but minus points for making the relationship feel pretty one-sided and glossing over the communication and boundaries that are so important to healthy ENM.
4. Missy
Meredith Grey will always earn a high spot on our lists. Both Chandler and Ross (David Schwimmer) had a crush on Missy Goldberg (Ellen Pompeo) back in college, even inviting her to watch their band, Way, No Way, play. They made a pact not to go after her, worried she’d become the Yoko Ono to their burgeoning music careers.
Fast-forward to a college reunion, and Ross asks Chandler’s permission to break the pact and ask Missy out. Chandler agrees, but when Ross tells Missy about their old pact, she reveals that she and Chandler had actually been secretly making out in the science lab after hours.
Betrayal! But we also love the fact that college Chandler was getting some action on the side.
3. Janice
Would we date Janice (Maggie Wheeler) ourselves? Not without some fantastic earplugs. But is she one of the most iconic characters to emerge from Friends? You bet. Find us someone who doesn’t immediately react to a nasal “Oh. My. God!” and then report back to us. And don’t even get us started on that laugh!
Chandler and Janice are on-again, off-again throughout the show, and despite the fact that he claims he can’t stand her, they have plenty of genuinely sweet moments. Janice supports him, surprises him with gifts, and clearly cares about him. Chandler hates that he loves her — but he really does.
Now for the bad (aside from Janice’s general demeanor): she cheats on Chandler with her ex-husband, the Mattress King. Boo, Janice! Chandler also rarely defends her to his friends, despite Janice repeatedly trying to win them over.
What really earns her a solid spot on the list, though, is the fact that they fall for each other all over again without even realizing who they’re talking to. Through an anonymous messaging platform, Chandler develops feelings for Janice based entirely on their typed conversations. Catfish potential? Absolutely. But also… kind of sweet.
And we can’t resist a woman in leopard print — and Janice was never afraid to double down.
2. Kathy
Now, this is a messy situation, so some might disagree with its placement on the list. But hear us out. Yes, Kathy is initially dating Joey, who met her just before Chandler could. Yes, Kathy and Chandler develop feelings for each other while she is still with Joey and should have come clean sooner. And yes, it nearly destroys one of the best friendships on the show. But putting all that aside… it remains a great storyline.
That betrayal gives us the famous box scene, featuring some of the best finger acting we’ve seen in our years— sorry, Mr. Darcy. We also love Paget Brewster from Criminal Minds and like to imagine this was just one of her undercover jobs where she got a little distracted from the case.
Kathy brings out a wonderfully caring and considerate side of Chandler, too. He tracks down an expensive first edition of her favorite childhood book, The Velveteen Rabbit, for her birthday. Then, in a very Chandler move, he lets Joey give it to her so she can receive it from someone — and she still figures out it’s from Chandler.
Terrified of disappointing Kathy, Chandler turns to Monica and Rachel for advice, giving us the iconic “7! 7! 7!” scene. He just wants to please her! A good man.
But the relationship ultimately falls apart when Kathy cheats on Chandler with her costar, Nick, after an argument where she’s offended that Chandler would even suggest she might do such a thing. Look, at least he was right?
1. Monica
Obviously, we were going to put Monica first. The people would riot if we didn’t. We’d get more hate than the actor who played Gunther after he got between Ross and Rachel.
Monica and Chandler are the ultimate friends-to-lovers story. They met through Monica’s brother, Ross, who was Chandler’s college roommate, but they didn’t become a couple until Ross and Emily’s wedding at the end of Season 4. A drunken Monica, offended after someone mistakes her for Ross’ mother, goes looking for Joey… only to find Chandler instead.
From there, we got the iconic turkey-on-the-head moment, the gasp-filled reveals to their friends, shark porn, and plenty more chaos from these two. Eventually, they get married, buy a house outside the city, and welcome twins through adoption.
But Monica and Chandler aren’t just a great couple because they make it to the end — and beyond. There’s no way Monica is letting that man go. It’s because they remain completely themselves while staying devoted to each other and their friendships. They soften each other’s edges without ever trying to change one another, and there’s such a deep sense of care and compassion running through their relationship.
Honestly, could they be any more perfect for each other?
